


Losing Your Virginity Series

by LeashedDemons



Category: Shall We Date?: Obey Me!
Genre: Closet Sex, Cunnilingus, F/M, Fingerfucking, First Time, Praise Kink
Language: English
Status: In-Progress
Published: 2020-12-08
Updated: 2020-12-08
Packaged: 2021-03-10 01:49:14
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 4,480
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27956426
Author URL: https://archiveofourown.org/users/LeashedDemons/pseuds/LeashedDemons
Summary: A series on you losing your virginity to the boys + unrelatables. The pronouns/descriptors used are for an afab!reader. Enjoy!
Relationships: Diavolo/Main Character (Shall We Date?: Obey Me!), Main Character/Mammon (Shall We Date?: Obey Me!)
Comments: 1
Kudos: 107





	1. Mammon

you couldn’t believe it.

it wasn’t exactly your first heartbreak but it _felt_ like the first one. you didn’t want to see anyone, didn’t want to do anything, even go to your RAD classes. the brothers had come to visit you, especially Lucifer, whom had assumed you were sick. it made sense, considering your refusal to leave your bed.

mammon was the most persistent - likely because he knew what had really happened. he visited you everyday, brought you food, made sure you ate it and tried to cheer you up. sometimes, he would just sit there with you in the comfortable silence, feeling the loss with you.

it had been days and you’d finally decided to get up, to shower, if only to _possibly_ erase the shame and embarrassment you felt. you stood under the water for hours and emerged _still_ feeling terrible. you felt **stupid** for falling for a demon and then it turning out as a _lie_ because, _of course it was_ right? you were surrounded by seven demons who didn’t lie to you and yet you still managed to find the one demon who manipulated you and fallen for him.

you barely dressed yourself, clad in only a white uniform shirt that you planned on sleeping in and made a beeline for your bed. you sat on the edge, hair still damp, and just stared down at the floor, wishing it would open you up and swallow you whole. you wanted to forget this ever happened, banish the feelings within you forever, but that wasn’t possible, even in the devildom.

the door opens, interrupting your thoughts and you already know who it is. it’s like clockwork - him showing up, bringing you leftovers he managed to save from Beel and spent time with you, talking about his day and shenanigans in hopes of bringing you out of this ‘funk’. you barely hear him come in, barely even notice as he sets a small plate of food on the nightstand, or even when he takes a seat beside you, denim-clad thigh brushing yours.

“doin’ better today?” he asks, but it’s a stupid question considering your current state. you sigh and lean against his shoulder, surprising him as he jumps at the action. you bury your face into the skin of his neck, inhaling the familiar scent of that _stupid_ perfume he always wears and you sigh at how comforting it is. you turn so you’re facing him and lean more completely into him, a hand coming up to gently grasp at his opposite shoulder. you _feel_ like you should cry, weep for what you’ve lost, but the comfort of mammon being this close to you is overwhelming.

“… _yeah_.” you exhale into his throat, the tips of your fingers lightly brushing the ends of his white strands. you inhale again, letting his scent wash over you as your fingers fist the jacket in your hands. it’s an unusually emotionally charged moment, one that you hadn’t really expected to have, especially with mammon. not to say that you didn’t feel a certain way towards the white-haired _idiot_ because you did — but it was never the right time, someone was interrupting, or in this case, you’d gotten your heart broken by a low-level demon. “mammon?”

“yeah?” he asks immediately, craning his head a little to look down at your face. you’re _sure_ you look terrible, only because you glanced at yourself in the mirror before coming out, but the look in mammon’s eyes makes you think otherwise. there’s a soft glow to his eyes as he looks down at you like he’s hanging on to _every_ word you say and it’s impossibly endearing, especially in your current state.

“don’t leave.” your fist tightens around his jacket and you feel him tense beneath you as you bury your face deeper into his neck, enough that your lips are mere _centimeters_ away from his throat. “stay with me, please. _please_ , mammon.”

he doesn’t know if it’s the way you’re saying his name so brokenly and with such need or the way you cling to him like he’s your lifeline but he hasn’t a mind to tell you no, not that he’d really planned on leaving anyway. of course, this was turning out a lot differently than he planned, but he wasn’t opposed to it’s direction.

a hand comes up to softly touch the back of your head, holding you to him and you feel nearly all tension leave your body as he runs a hand over your head, rubbing it soothingly. you sigh, breath tickling his throat and goosebumps rise across his skin. he rubs your head again, pressing a kiss to your temple and then pulling away to look down at you.

an electricity sparks as your eyes meet. it’s the proximity, the veil being lifted from each other’s eyes, the _finally_ being alone - all of it adding up to an intense atmosphere that leaves you struggling to breathe as you can’t figure out what to do. you _want_ to kiss him, but does he want to kiss you?

his golden eyes move from your eyes to your lips then back upwards as his hand finds the side of your face, pulling you in without you realization what’s happening. in mere moments, one of your many daydreams has come true as mammon’s lips press to yours in a hesitant kiss. he waits, testing to see if you wanted this as well and when you release his jacket to grab the back of his neck, he presses deeper into the kiss.

your head tilts as his does too, kiss deepening and welcoming his tongue into your mouth. your back meets the mattress, mammon on top of you, and your awful feelings are slowly fading. he steals a kiss from you, then another, and another, _and another_ until you lose count and your mouth is dry. you don’t care, instead pulling him into another kiss, pulling him down against you.

mammon is a bit surprised by the reciprocation, more so the _intensity_ but doesn’t argue or resist, letting his body mold to yours like it was meant to be there, _like he was made for you_. you know there’s going to be repercussions, _consequences_ of doing what you’re doing right now but you don’t care, not then, not in that moment.

“mammon…” you start again, gathering yourself for what you’re about to say. it’ll be more shocking to him, but you have a feeling that considering your current predicament that he won’t decline. fingers wind into his white hair and you pull away, though keeping close as your breath lingers with his. “i…i want you to be my first.”

“wha?” he immediately asks, though not necessarily at your request. more so at the face that you hadn’t _done this_ _before_. you’re the most beautiful human in his eyes, eclipsing even demons, and he can’t believe that someone has never kissed or held you like this. it excites him a little bit to know that you want him to be your first - to show you the world of pleasure that awaits. “a-are you sure?”

you kiss him in reply, lifting your legs to wrap them around him. you _might_ regret this tomorrow, but you might not and your heart is holding out for the latter. mammon kisses you deeply, one of his hands winding beneath you to embrace you to him. his opposite hand starts to wander, though you don’t leave much to imagination in your white button-up.

“mammon.” you whine, tugging at his jacket, feeling he is _massively_ overdressed. he chuckles, pulling away from you to lean back on his haunches as he shrugs out of the jacket. his shirt goes up and over his head, following the same path as his jacket.

he’s pressing himself against you again and you feel his hands start to undo the buttons of your shirt, a soft sigh leaving your lips at the skin-on-skin contact. you wrap your arms around his shoulders, hands exploring the skin of his back. he groans, releasing your lips to start to kiss your neck, sucking on various spots. you _know_ you’ll be marked up tomorrow but it only makes you feel hotter, _needier_.

“ _mammon_ , please.” you plead, grasping his hand and burying it between your plush thighs. he considers teasing you, but decides there will be time for that _next time_. his fingertips softly stroke your lips, already feeling them starting to get wet. he softly strokes you a few times, gathers your slick and then gently breaches you with his middle finger.

you gasp at the intrusion, your pussy clenching around his finger and you cling to his shoulder as he starts to slowly thrust it in and out of you. you find something, _anything_ to anchor you as he starts to gradually bring you to your orgasm and your hand finds the sheets beside you, fisting the material in your hands.

“f-fuck, _ah_.” you throw your head back, closing your eyes as his pace increases. you feel your breathing get ragged, your chest heaving, and your hips start to meet his hand. his hand continues to undo the buttons on your shirt, _somehow_ only requiring one hand to do so. he shoves the shirt open and you’re crying out as his mouth descends on your chest, sucking on the skin of your breast before taking the nipple into his mouth. “oh **fuck** , mammon.”

“mhm.” he moans around your nipple and you feel him slide another finger inside of you with ease, your dripping pussy accepting him with ease. you can feel your orgasm approaching, getting closer and closer with every press of his fingers against your soft, clenching walls and you _almost_ went to put it off. before you can even say anything of the sort, mammon’s thumb presses against your clit and starts to rub it, bringing you to the most intense orgasm you’ve ever achieved.

he withdraws his fingers from you and it takes you a few moments to come down from your high, peppering your body in kisses as you do so. he kisses his way back up your body and you envelop him in an embrace as you kiss him, feeling his erection now fully hard against your thigh. you reach between your bodies and palm him through his jeans and he shudders above you.

you seize the opportunity to change your positions, flipping him so that he is instead beneath you. your hand dives beyond his waistband, grasping his cock as you realize _mammon is commando_. you start to slowly stroke him, or what you can grasp of him from your position. mammon is shivering, panting into your ear as you touch him and as you run your finger over the slit on the top, he _moans_ into your ear.

it’s so utterly sexy that if you weren’t wet before, you are now. you keep stroking him, able to feel him throb in your hands as he trembles above you. Just as you feel he might release into your palm, mammon grasps your wrist and pulls it out of his pants, pinning it beside your head.

“s-supposed to be makin’ you feel good, stupid human.” he mumbles somewhat brokenly, still panting from the effect your touch had on him. slowly, he uses his opposite hand to tug his jeans down, just enough that his cock is sprung free. then your legs are lifting, wrapping around his waist in anticipation of what’s to come. “r-ready?”

you feel his tip press against your entrance and you wiggle, desperate to have him inside of you. you nod, grasping his face and pulling him down into a searing kiss, tongues mingling. he uses this moment to slide inside of you, swallowing your surprised gasp. you recognize that feeling everyone talked about - the feeling of being stretched, though it wasn’t very painful, more so uncomfortable. it’s bearable though and you want mammon badly enough that you’re already lifting your hips to meet his.

mammon sees this as a sign that you’re ready, slowly dragging his cock out of you and then back in again. the second time is a lot better than the first and the feeling is starting to subside. your hand instinctively braces against mammon’s shoulder, the other grasping at his side as he starts to pick up pace - his golden gaze concentrated on you as you two become one.

“a…o-oh…M-Mammon.” your words come out broken, his thrusts completely destroying your line of thought. your gasps and moans start to increase in volume as his pace increases, keeping up with the sound of squelching and skin meeting skin again and again. your nails dig into his side and he hisses, leaning down to capture your lips again.

“does that feel good, _my human_?” he murmurs against your lips and you nod brokenly, not even sure of what you’re saying - your mind just connecting the words _good_ to what you’re feeling. he grins, fangs bared as he leans into your throat again. this time, he surprises you by sinking his teeth into your neck.

the pain hits you first, causing to gasp and nearly pull away but then the pleasure of both his bite and thrusts has you clamping your eyes shut and calling out for him, nails digging even deeper into his side. he withdraws, looking satisfied at the reddening mark on your throat and returns to kissing you, his hips snapping into yours at a nearly inhuman pace at this point.

“let me make ya feel good. let me make ya come.” he murmurs against your lips, silencing your moans as they get louder with the intensity of the warmth in your belly. it’s like moments before when he was fingering you, only _thousands_ more intense. you feel like you’re burning with the heat of a thousand suns, ready to burst at any moment and as mammon thrusts inside you again, you feel him hit something deep, something you’ve never even touched before within yourself. you half-yelp, half-groan, your noises on par with a porn star at this point.

mammon grins at your noise and adjusts, lifting one of your legs up to rest against his chest, allowing him to hit that spot once more when he slides inside of you.

“cum for me.” he moans into your ear and you come undone immediately. your head falls back, back arching into him and mammon watches your reaction with a greed befitting only him. he’s following you only moments later, his cum filling your insides. you briefly think that _maybe_ wearing protection would’ve been a good idea but you’re too busy basking in your post-coital bliss to care.

mammon collapses against you, covering your face and neck in kisses. you sigh, draping your arms around him and holding him against you. you’re utterly exhausted, eyes already feeling droopy as you hold him to you. you feel him shift on top of you and then something soft fall on top of you, presumably the blanket. he lays down beside you and pulls you against him, your arm falling across his chest. he presses a kiss to your forehead and whispers.

“ _my human_.”


	2. Diavolo

you don’t know exactly how you ended up in this situation with the demon prince, but you’re not very sure that you minded. it had stated as a simple tea meeting and somehow snowballed into a game of hijinks in which you were playing miniscule pranks on his lovely butler, Barbatos. _that_ was how you’d ended up in this rather tight closet with the ridiculously huge prince of Devildom, Diavolo.

you both wait with baited breath, mostly Diavolo because literally every time he breathes, you’re pressed against the opposite side of the closet. you hear Barbato’s steps coming and you don’t know why but you grab onto the prince’s shoulder or try to, only grasping his arm with the difference in your heights and stiffle a giggle. he smiles at you, waiting as the footsteps approach, stop briefly in front of the door and then depart.

“ _we did it_!” you whisper-yell, pressing yourself against Diavolo’s arm as you hear Barbato’s footsteps fade. Diavolo looks to you and grins, turning to face you, his own hands coming to grasp your shoulders as he beams with excitement. it’s only then that you really realize exactly how _small_ the closet is. there isn’t any room to move except side-to-side or against each other. getting out would be difficult.

“i can see why Lucifer likes you, Y/N.” Diavolo says, still holding some of his breath in to prevent you from quite literally being squished. you feel yourself grow flush at his words. his slow, ragged breath fills the closet for a moment before he speaks again, a flush visible on his cheeks. “the more i know about you, the more drawn to you i feel. nothing can captivate me as you do.“

you’re not sure what to say - this sounding like one of those love confessions in Levi’s animes but there is still room for interpretation to what Diavolo’s saying, at least in your mind anyway. he _could_ mean you captivate him like food captivates Beel; granted, you’re really _hoping_ that’s not how he means it.

Diavolo seems confused by your lack of response, one large hand coming up to softly cup the side of your face and tilt it back, bringing your (e/c) eyes to meet his light golden eyes. he stares at you for a few moments, just memorizing the lines of your face, the color of your eyes and the way your lips twitch at the sight of his.

he’s leaning forward then and in a shocking moment of dreams made reality, your lips are against the soft ones of the prince of Devildom. it starts as a light kiss, just a peck on the lips, but then you’re surging forward and connecting your lips again. he’s kissing you with an intensity you hadn’t known before and the breath he’d been holding is released - that vast chest of his pressing you against the wall as your hands find those long dark red strands of his.

“a-ah…d-dia…” you manage to mumble out as you’re hitched up the wall by his hands finding your waist and lifting you. you wrap your legs around him immediately, feeling a hardness probing you through your panties. you realize that today might be the _one_ day you’re thankful for the skirt of your RAD uniform. “w-wait…”

he immediately pulls away from you, though still holding you against the wall. you’re perfectly level with his face, your small hands clasping onto his hulking shoulders as he stares at you with a look of concern ironic for the future King of Devildom. his face is still flushed, even more so in that moment as he averts his gaze a little.

“my apologies, Y/N, it seems i got…carried away…” he murmurs, gaze falling to your throat. despite his words, the hunger in his eyes remains and you wiggle a little in his arms, moving to link your hands behind his neck. your hands card through his dark red hair, smiling softly.

“that’s not it, dia…” it’s your turn to flush because of the admission you’re about to make. you worry it could change his opinion of you, as it has before and you can’t help the frown that comes to your lips. “i…i’m a virgin…”

his golden eyes illuminate even further at your revelation, moving from your neck to your face. instead of being repulsed or upset by this new reveal, he almost seems more excited by it. it makes you look away beneath his heated gaze, but Diavolo shocks you by pressing an intense kiss to your lips.

you don’t hesitate to kiss him back, letting him swallow your noises as his tongue snakes into your mouth. you’ve never been kissed like this before, never so intense, or with such _desire_ but you never want him to stop. your tongues linger together as Diavolo explores your mouth, getting acquainted with it before pulling away, an intense and serious look on his face.

“Y/N, if you would allow me…” leave it to Diavolo to sound so proper while he has you against a wall, literally kissing the life out of you. “I would be honored to be your first.”

“Y-yes… _please_ , Dia.” you reply without hesitation and he kisses you again, this time with a more intense desire than before. you feel him shifting you and then a knee presses between your thighs and you gasp, not even realizing how utterly soaked you already were. your body has a mind of it’s own, hips starting to work against the thickness of Dia’s thighs and you’re shuddering at the sensations it’s giving you.

you’d touched yourself before and even had a few intense make out sessions with past lovers, but never had it felt like this. never had you wanted someone like you wanted Diavolo in that moment. his hands tighten around your waist, starting to work you slowly against the leather material covering his thigh.

“f-fuck, Dia…” you whine and he shifts, pressing his knee more urgently against your heated center. Diavolo is clearly more experienced than you - nearly bringing you to orgasm with just his knee and you only grow more excited every second, eager to see what else he has in store for you. “i-it’s too much.”

as if remember that you weren’t his typical demon lover, he stops his ministrations and just _pants_ against you. you realize then just how much he’s holding himself back and while a part of you just wants to tell him to let loose on you, but you know you can’t handle it at this point. would there be a next time, you wonder?

while you’re thinking this, Diavolo is suddenly setting you down and sinking to his knees, hands grasping your thighs and tossing them over his shoulders. he pushes your panties to the side and his tongue is lapping up your essence. you gasp at the sudden sensation and your knees would be buckling if it weren’t for him holding you up.

“does that feel good, Y/N?” he asks, but he _knows_ the answer. he knows how good he’s making you feel as you’re literally _dripping_ on his tongue, begging to be touched, _to be fucked_ and he’s struggling not to just take you then. he has to _prep_ you for him, being as virginal as you are and how large his cock is.

“i… _please_ , dia.” you can’t take it anymore. you feel like you’re about to burst and you need him. Diavolo seems to want to prep you more, but he can’t control himself either. he stands, keeping one hand braced on your waist to hold you up and it’s only a measure of his strength as he holds you there while he practically rips open his belt, unzipping his pants to free his monster cock, already dribbling with pre-cum.

you’re stunned, both at the size and the thickness and _sweet Diavolo_ , maybe you weren’t ready. would it even fit? you worry that he could prep you for hours and it still wouldn’t be enough. Diavolo notices your concern and softly cups the side of your face, pressing a kiss to your face.

“i’ll go slow, Y/N. i promise.” he assures and kisses you again, sliding into you at the same time. you feel his head breach you and you would shriek at the feeling, if it weren’t for Diavolo’s mouth on yours. He swallows your sounds as he starts to press deeper inside of you.

it sort of feels like you’re being split in half on his cock, but the pleasure far outweighs the pain. it takes a few moments for the pain to subside and he’s only _half_ inside of you, but your hips are already jumping to take him deeper. you’re whining, hips wriggling as he sinks deeper inside of you and your head falls back, not even caring that you hit your head on the wall in doing so.

“oh, _fuck_ , Dia!” you cry out, a little louder than you intended but you can literally feel his cock brushing against your clit as he sinks deeper and it’s driving you crazy. your hands tighten around the shoulder of his uniform and Dia groans, not realizing _just how_ tight you’d be.

“Y/N…you’re so…so…tight…” he mumbles and while it sounds so _dirty_ to your ears and causes a rush of heat to your core, he’s only commenting on how you’re squeezing around him and struggling to take him deeper and deeper. “feel so good…positively… _divine_ …”

he buries his face into your throat as his hips start to snap in and out of you, Dia’s hands holding your waist as he literally bounces you on his cock. it’s not exactly how you imagined your first time but you wouldn’t have it any other way. his arms enclose your waist, holding you to him in a borderline bruising hold as he becomes erratic in his thrusts.

“o-oh…ah, Dia!” you whine, your orgasm building and _building_ like a fire in your stomach. Diavolo only stokes the fire as one of his hands grasps the front of your still-buttoned shirt and tugs, buttons flying everywhere as your chest is bared to him. he starts to kiss and suck at your chest and your body tenses, orgasm rapidly approaching. “Di-Dia…i’m…i’m gonna-!”

it’s all you manage to get out before your orgasm hits you like a wave and Diavolo presses his lips to yours to silence your scream of his name, groaning as you clench around his cock even tighter than you had before. these two things combined are enough to push him over the edge as well and you feel him spurt his cum inside of you before either of you can think of him pulling out.

you collapse in his arms, limp as a noodle, and Dia withdraws from you slowly, chuckling a little at the soft whimper that leaves your lips. he fixes your panties and holds your exhausted form against him, running his long thick fingers through your hair. he presses a kiss to your forehead.

“i don’t think i’ll ever be able to let you go, Y/N.” he murmurs and you smile, weakly but still, it’s a smile. you grasp at his shoulder and tilt your head back so you can look at his face, the glow of his face visible even in the closet.

“take me to bed, Dia.” with that, you lay your head against his chest and the last thing you remember is him opening the door and the sound of Barbatos yelling at him for being gone so long.


End file.
